Michael McMillian as Tom Reinhart

Hilary Duff as Lane Daniels

Amanda Walsh as Joanne

Chris Carmack as Liam

Jaime Pressly as Kate White

Jennifer Coolidge as Alicia

Billy Slaughter as Accountant

James McDaniel as Mr. Belmont

Matt Dallas as Seth

Kevin Kirkpatrick as John

Lyle Brocato as Waiter

Alix Angelis as Aspiring Assistant

Carol Sutton as Recruiter

Courtney James Clark as Margo

Brandi Coleman as French Model

Tarik Naim Alherimi as Rodrigo

Patricia French as Bored Fashion Editor

Dean J. West as Accountant #2

Lacey Minchew as Whitney

Edrick Browne as Junior Analyst Eddie

Scott M. King as Businessman (uncredited)